


The Wisdom of The Winchesters

by LuckyBanana



Category: Supernatural
Genre: Bro bonding, Explicit Language, Explicit Sexual Content, F/M, Humor, Innocent Castiel, Non-Explicit Sex, Reader-Insert
Language: English
Status: Completed
Published: 2016-01-17
Updated: 2016-01-17
Packaged: 2018-05-14 11:05:29
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,394
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/5741350
Author URL: https://archiveofourown.org/users/LuckyBanana/pseuds/LuckyBanana
Summary: <blockquote class="userstuff">
              <p>Castiel seeks some "relationship" advice from the sexual dynamic duo known as Sam & Dean Winchester.</p>
            </blockquote>





	The Wisdom of The Winchesters

Dean chose a beer cap from his substantial pile and flung it at Sam. Sam laughed and chucked it back at his brother. Outside, an unusually heavy snowfall covered the stark landscape surrounding the bunker. Weirdly, even demons took a break when it was cold outside. Left without a case for a couple of weeks, the boys were bored and restless. 

Dean put his feet up on the large table and sighed. “Where’s Y/N? We should play some poker or something.” 

Sam looked up from his laptop. “She’s still out,” he said. 

“Where’d she go?” Dean asked, annoyed. 

Sam just shrugged his shoulders and went back to his research. Suddenly, the air of the bunker was disturbed by the distinct fluttering of wings. 

“Thank God,” Dean looked over to the angel who had just materialized. “I’m fucking bored. Cas, what’s up. Is there trouble?” 

Castiel frowned. 

Sam noticed that their celestial friend looked different. He was wearing a tailored suit, his beige trench coat was freshly laundered, and his hair was uncharacteristically tidy. Despite his impeccable appearance, Sam could see that Castiel was distressed. Sam closed his laptop. “You okay, Cas? What’s up?” he asked.

“Is Crowley up to something again?” Dean asked as he got into attack mode.

“No, no. It’s nothing like that.” Cas replied. He looked down at his feet and began to shuffle around awkwardly. “I need…some advice. About a woman.” 

Dean looked very serious…for about five seconds. Then he dissolved into hysterical fits of laughter. “You need dating advice?” he gasped. “Oh my God, that is precious! Castiel has a girlfriend! AH HAHAHA…” 

Sam furrowed his brow as the angel turned a bright red. “Dean shut up! Don’t be a jerk!” Sam said. “Of course, ask us anything you want.” 

Dean regained his breath. He got up and slapped Castiel on the back. “Way to go, dude. Congrats! You finally popped your cherry!” 

Castiel swallowed but said nothing. 

“Or…not. THAT’S what you need advice about?” Dean began. “Well, sometimes when a man and a woman like each other very very much, they share a special kind of hug…” Dean began making obscene gestures with his fingers. 

“I know how everything works, Dean. Physiologically, anyway…” said Cas.

“Ah…” Dean sat down again. “So, you need advice on how to make your lady ‘happy’? Well, you came to the right place!” Dean crossed his arms, looking very pleased with himself. “But first, you gotta tell us. Who’s the lucky lady?”

Castiel’s eyes darted between the brothers, unsure how to proceed. 

Sam cleared his throat and interjected. “That’s really none of our business Dean.” He was trying to be sympathetic. It was obvious to him who the lucky lady was. Sam noticed how the angel looked at you. It was totally obvious that Castiel adored you, obvious to everyone but Dean. 

Castiel could see that it was useless to try and hide it. “Y/N and I have been…seeing each other.” he said at last. 

“WHAT?” Dean yelled. “YOU and Y/N?? Eww!!”

“Don’t listen to Dean! He’s just angry because he can't decide which one of you he’s jealous of.” Sam said as one of Dean’s beer caps collided with his forehead. 

Castiel looked like he was about to cry, so Dean resigned himself to be serious. “Look, I’m sorry I’m such an asshole.” Dean said. “You’re a lucky man, really.” 

“I know that I am.” Castiel said as he took a seat at the table. “I’m just a little…overwhelmed. I have never felt this way before, about anyone, or anything. It’s very…human, and…visceral.” 

Dean pulled a face, but urged Cas to continue. “So, what are you worried about?” he asked. 

“Well, we’ve kissed.” Castiel turned a deeper crimson. “And, I want things to go further, but I’m not sure…what to do. I don’t want to displease her.” 

Sam realized that he had never seen the angel embarrassed before. His heart when out to him. “Well, you’ve just got to go with the flow, and see what happens. Don’t rush it.” Sam offered. 

“That’s all very vague, Sam.” Cas frowned. “As I said, I know…where everything goes, but… I have watched those videos that Dean tries to hide, and it all seems so…aggressive.” 

Dean concentrated on picking at the label of his beer bottle. “You didn’t watch the one called _Red-Head Cheerleader Loves It All_ , did you?” he asked.

Castiel nodded. 

It was Dean’s turn to be embarrassed. “Yeah, that might be the wrong approach. If you try that with Y/N, she’ll rip your head off,” he said. 

Sam rolled his eyes. “You can start by undressing her.” Sam said. 

“And let her undress you,” Dean added. 

“Don’t forget to kiss her,” said Sam. 

“Enjoy touching her.” 

“Be gentle.”

“But don’t be afraid to be forceful if it feels right.” 

“Communicate with her, consent is sexy…”

“…and mandatory.” 

“Be giving.”

“Tell her what you want.”

Castiel’s head flicked from brother to brother like he was watching a tennis match. He furrowed his brow, trying to absorb the barrage of information. 

Dean continued, “Make sure to warm her up. Ladies come first, ALWAYS. And often, if you can manage.” he smirked. 

“Go slowly, tease her,” contributed Sam.

“Watch her for signs that you’re making her happy. If she pulls your hair out, you’re doing something right,” said Dean.

“Be…” Sam was cut off by the sound of the bunker door crashing open. 

“Fuck, it’s cold out there!" You entered the room, shaking the snowflakes from your hair and peeling off your thick wool jacket. “Oh, hello Castiel!” You tried to hide your surprise at seeing your date sitting in your kitchen. 

Cas looked at you with a slightly pained expression. You felt like you had just walked into a room where a bunch of nerds were just having a conversation about you. You frowned hard at the men sitting around the table. 

“What is going on?” you frowned harder. 

They stared back at you like a bunch of idiots for a full minute before Dean erupted into a fresh fit of hysterics. Sam joined in his brother’s mirth and you swatted Castiel on the shoulder.

“Dammit, Cas!” you cried. “If you were going to tell them, you could have at least given me a ride home! Or a teleport home…or whatever.” 

“We know you guys are smooching boots!” Dean regained his breath in time to tease you.

“I’m so sorry, Y/N.” Castiel flashed you his puppy dog eyes. 

“Yeah, whatever, so the jig is up! Thanks for a great evening anyway, Ladykiller.” you said and leaned down to give Castiel a passionate, open mouthed goodnight kiss. 

Dean started giggling anew as you swaggered up the stairs to your bedroom. 

The three men watched your back as you swayed up the stairs in your sexy black evening dress. Castiel cleared his throat to break the brothers out of their reverie. Sam redirected his attention to the innocent angel. 

“Be a gentleman,” whispered Sam. 

“But make her beg for it,” mumbled Dean.

“Be yourself.” 

“But be her fantasy.”

“But most of all…”

“DON’T OVERTHINK IT.” 

***  
5 am, and the sheets under your naked bodies were soaked through. Your eyes swam with sweat and tears of giddy pleasure. Your body tingled and your pulse throbbed in the place between your legs. Your muscles ached with sated exhaustion. You turned your head to look into the face of your lover. Through heavy eyelids Castiel looked back. 

“Where…did you learn…how to do that?” you croaked. 

“Let’s just say, I had some good advice…” Castiel purred as he kissed you deeply, once again lowering his body into yours. 

***

Dean yawned and looked out the bunker window. He guzzled his coffee like it was his lifeblood. Sam, resplendent in bed-head, padded out to the kitchen, nodding a sleepy salutation to his brother. He helped himself to a cup of steaming brew. Suddenly, the silence of the morning was broken by a deep moan. The boys regarded each other with mouths open. The moan grew louder and transformed into a guttural cry of intense pleasure. Dean raised his eyebrows but said nothing. His expression changed from bewildered to impressed. The boys clinked their coffee cups together in mutual recognition of a job well done.


End file.
